Margaritaville, Rolling Oaks Homes with Two Story Style

Margaritaville, Rolling Oaks Homes with Two Story Style

Welcome to Margaritaville, Rolling Oaks – a vibrant community nestled in the heart of Kissimmee, Florida, where the sun shines brightly and the spirit of relaxation is always in the air. This enchanting subdivision is part of Osceola County and offers an idyllic blend of modern living with a laid-back, tropical vibe that’s perfect for families, retirees, and everyone in between.

Margaritaville, Rolling Oaks is renowned for its stunning two-story homes that exude charm and sophistication. These residences are thoughtfully designed to maximize space and comfort, featuring open floor plans, spacious bedrooms, and inviting living areas that are perfect for entertaining friends or enjoying cozy family nights. With ample natural light pouring in through large windows, each home feels warm and welcoming, making it a true sanctuary for its residents.

The community itself is a treasure trove of amenities, offering residents access to lush green spaces, sparkling pools, and recreational facilities that encourage an active lifestyle. Imagine spending weekends lounging by the pool, taking leisurely strolls through scenic pathways, or hosting barbecues in your backyard while enjoying the balmy Florida weather.

Located just a stone's throw away from world-famous attractions like Walt Disney World and Universal Studios, Margaritaville, Rolling Oaks is the perfect place to call home for those seeking both adventure and tranquility. With its unique blend of resort-style living and family-friendly atmosphere, this subdivision is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover your dream home in Margaritaville, Rolling Oaks – where every day feels like a vacation!

Newest Margaritaville, Rolling Oaks Homes with Two Story Style

$315,000
2 Beds ⋅ 3 Baths ⋅ S5155480 MLS ⋅ 8201 BLDG.
Welcome to paradise at 8201 Surf St, a beautifully appointed, fully furnished 2-bedroom, 2.5-bathroom townhome offering the ultimate turn-key resort lifestyle. Nestled in the heart of the world-class Margaritaville Resort Orlando, this property boasts a prime location on the same street as the signature cottages and stands as one of the closest units to the main hotel building and its sprawling resort-style pool complex. Step inside to an inviting, open-concept floor plan filled with tropical charm and modern finishes, seamlessly extending out to a private patio area perfect for enjoying warm Florida sunshine, morning coffee, or evening relaxation. Positioned for exceptional investment potential, this home generated $45,587.00 in rental revenue for 2025, making it a proven performer for savvy real estate investors or buyers seeking an income-producing personal vacation getaway. Owners and guests enjoy top-tier resort amenities, including the zero-entry pools at Fins Up Beach Club, the tranquil St. Somewhere Spa, poolside dining at Salty Rim Bar & Grill, a state-of-the-art fitness center, and access to the adjacent Promenade at Sunset Walk and Island H2O Water Park. Located just minutes from Walt Disney World, Universal Orlando, premier shopping, and world-class dining, this move-in-ready property delivers effortless island living and lucrative return potential in Central Florida’s premier destination.

8201 Surf Street, Kissimmee
$359,999
3 Beds ⋅ 3 Baths ⋅ S5149980 MLS ⋅ 2916 BLDG.
Welcome to paradise at 2916 On The Rocks Pt, a stunning, turnkey-ready 3-bedroom, 3-bathroom townhome located in the highly coveted Margaritaville Resort Orlando. Sold fully furnished and beautifully decorated, this property features a bright, open-concept living area that seamlessly transitions to your own private patio space—perfect for soaking in the warm Florida sunshine. Best of all, you are just steps away from one of the pristine community pools. Designed for effortless ownership, this property is an exceptional opportunity for vacation home buyers seeking a personal tropical getaway or savvy investors looking to capitalize on a premier short-term rental destination. Living in Margaritaville Resort means enjoying a world-class, island-inspired lifestyle with access to incredible amenities, including expansive lagoon-style swimming pools, the relaxing St. Somewhere Spa, a state-of-the-art fitness center, and the thrilling Island H2O Water Park. The property is also exceptionally close to the Promenade at Sunset Walk, a bustling hub packed with premier dining, retail shopping, and live entertainment. Located just minutes away from Walt Disney World Resort and other top Central Florida attractions, this townhome offers the ultimate blend of resort relaxation and theme park adventure.

2916 On The Rocks Point, Kissimmee
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